Bootleg & Barrels: A Tennessee Whiskey Tasting Experience

Travelers with a taste for history and a penchant for good spirits will find the Bootleg & Barrels tour in Nashville offers a compelling mix of storytelling, hidden bars, and top-notch whiskey. This 2-hour walking experience isn’t just about sipping—it’s about unraveling the wild tales of Prohibition, gangsters, and Nashville’s secret liquor scene.

What makes this experience stand out? First, the expert guides trained in whiskey tasting bring authenticity and knowledge that elevates the tour beyond your average bar crawl. Second, the exclusive access to some of Nashville’s most iconic and hidden tasting rooms provides a genuine, less touristy perspective. Lastly, the storytelling is filled with true crime, folklore, and scandalous tales—perfect for those who crave entertainment along with their drinks.

Of course, a potential consideration is that tasting is not included in the tour price, so you’ll want to budget for drinks at each stop if you’re thirsty. But if you enjoy learning about history while discovering Nashville’s secret bars, this tour hits the mark. It’s especially well-suited for whiskey lovers, history buffs, or anyone intrigued by the outlaw days of Tennessee.

Good To Know

• Authentic storytelling brings Prohibition-era Nashville to life.
• Curated whiskey tastings at hidden and iconic bars.
• Expert guides trained in whiskey tasting provide insights you won’t find elsewhere.
• Walking tour with a focus on history, crime, and folklore.
• Price offers great value for the personalized experience and exclusive access.
• Age restriction is 21+ with alcohol available for purchase.
• Rain or shine — dress accordingly for a walking adventure.
• Flexible cancellation up to 24 hours in advance.

You can check if your dates are available here:

An In-Depth Look at the Experience

The Tour Overview

Starting point at the Standard Proof Whiskey Company, this tour is designed for those who want to combine history, storytelling, and whiskey in a lively, engaging way. The duration is two hours, generally scheduled in the afternoon or evening, giving flexibility around your Nashville itinerary.

The price point of $38 per person might seem modest, but it reflects the experience’s focus on storytelling and exclusive bar visits rather than an all-inclusive tasting. The value lies in the knowledgeable guide, the hidden locations, and the stories that make Tennessee whiskey unique.

What to Expect During the Walk

From the moment you meet your guide—who is not only well-versed in whiskey but also a storyteller—you’re transported into the shadowy days of Prohibition. The tour’s theme revolves around outlaw legends, secret speakeasies, and scandals that shaped Tennessee’s liquor history.

Your guide will lead you through some of Nashville’s most iconic and secret spots, sharing stories of moonshiners dodging revenuers, powerful families controlling the liquor trade, and murder and betrayal in the shadowy underworld of the South. These tales are complemented by visuals, period costumes, and the atmosphere of each bar.

The Bars and Tasting Rooms

The stops are carefully curated for their historic significance and ambiance. You’ll visit places that exude the grit and glamour of Prohibition-era Nashville—bars that have survived the test of time or have been restored to evoke their clandestine pasts.

While tasting isn’t included in the tour fee, each bar offers a curated selection of Tennessee spirits, which guides will describe, providing context about the different types of whiskey and their histories. Reviewers mention that the flight tasting at Standard Proof Whiskey Company is a highlight, even if the eight half-ounce shots can feel a little overwhelming at the start. It’s a good idea to pace yourself.

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The Storytelling

What sets this experience apart? The guides are described as knowledgeable and entertaining, with one reviewer claiming they were the “best guide ever.” Their ability to weave tales of murder, political corruption, and gangland brawls makes the history come alive. You’ll hear about underground distillers, families who ruled Nashville’s liquor trade, and the scandals that shook the city.

One traveler appreciated the personalized touch, mentioning that during a private tour, they could ask questions freely. This suggests that smaller groups or private experiences might be available, enhancing the intimacy of the storytelling.

Practicalities

Dress code is somewhat formal; avoid cut-offs or distressed clothing, and gentlemen should wear shirts with collars. The tour is a walking experience, so comfortable shoes are recommended. Since the tour is rain or shine, bringing an umbrella is wise.

Alcoholic beverages are available for purchase but not included in the tour price. You can buy drinks at each bar, which are set at their own prices, so budgeting accordingly is sensible. The tour is suitable for those 21 and over, and proof of age is required.

The Value Proposition

For $38, you get a guided walk through Nashville’s whiskey and criminal history with an expert who makes the stories engaging and memorable. The combination of exclusive access, storytelling, and curated tastings offers good value—especially if you love learning while sipping.

Several reviewers appreciated the personalized experience, noting that the guide’s storytelling was both informative and lively. One traveler even called the guide “knowledgeable and entertaining,” which indicates a high level of expertise and charisma.

Who Will Enjoy This Tour?

This experience is perfect for whiskey lovers eager to learn about Tennessee’s distilling past. It’s also ideal for history buffs interested in the Prohibition era and Nashville’s underground scene. If you’re looking for a fun, interactive way to explore the city’s hidden bars, this tour is a great fit.

It’s less suited for those who prefer all-inclusive tastings or who aren’t interested in walking and outdoor exploration. Also, travelers under 21 won’t be able to participate in the tasting aspect, though they can still enjoy the stories and scenery.

The Sum Up

Bootleg & Barrels offers a distinctive look into Nashville’s past, blending entertaining storytelling with curated whiskey experiences in some of the city’s most iconic and secretive locations. The focus on history, crime, and legendary figures makes it stand out from typical tasting tours.

The guides’ expertise significantly enhances the experience, making learning about Nashville’s outlaw days as engaging as sipping a fine Tennessee whiskey. While tasting isn’t included in the base price, the opportunity to explore hidden bars and hear captivating tales more than compensates.

This tour is best suited for adventurous travelers who appreciate a good story and want a deeper understanding of Nashville’s complex relationship with whiskey. Whether you’re a seasoned bourbon enthusiast or a true crime aficionado, this experience promises a spirited journey through Tennessee’s rebellious past.

FAQ: Your Questions Answered

Is the tour suitable for non-drinkers?
Yes, you can participate in the walking and storytelling aspects without tasting, but alcohol consumption is optional and age-restricted to 21+.

How long is the tour?
The experience lasts approximately 2 hours, typically scheduled in the afternoon or evening.

Where do we meet?
Meet in the lobby of the Standard Proof Whiskey Company, which serves as the starting point.

Are drinks included in the price?
No, alcoholic beverages are not included. You can purchase drinks at each bar, with prices set by the bars themselves.

Can I cancel my reservation?
Yes, you can cancel up to 24 hours before the start for a full refund, providing flexibility for travel plans.

Is this tour suitable for large groups?
While the reviews mention private tours, the standard experience is designed for small groups, ensuring personalized storytelling.

What should I wear?
Dress smart casual—avoid overly distressed clothing and flip-flops. Comfortable shoes are recommended for walking.

Can I take photos during the tour?
While not explicitly stated, most guided tours allow photos of the historic locations. Respect any bar policies regarding photography.

In sum, Bootleg & Barrels is a lively, authentic way to uncover Nashville’s secret past, with expert guides making history both fun and memorable. It’s a splendid choice for those who want a taste of whiskey and a story or two to share long after the last sip.

You can check if your dates are available here: